Synthesis of the enantiomers of 6-epicastanospermine and 1,6-diepicastanospermine from D- and L-gulonolactone.
The synthesis of the enantiomers of 6-epicastanospermine and of 1,6-diepicastanospermine from the enantiomeric gulonolactones is reported and the structure of the former is established as (1S,6R,7R,8R,8aR)-1,6,7,8-tetrahydroxyoctahydroindolizine. The inhibitory activities of the diastereomers against the amyloglucosidase-catalysed hydrolysis of p-nitrophenyl alpha-D-glucopyranoside were investigated, and the effects of 6-epicastanospermine and of 1,6-diepicastanospermine on 14 human liver glycosidases are reported.
Fleet
G W
GW
Dyson Perrins Laboratory, Oxford University, Great Britain.
Ramsden
N G
NG
Nash
R J
RJ
Fellows
L E
LE
Jacob
G S
GS
Molyneux
R J
RJ
di Bello
I C
IC
Winchester
B
B
D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006801:Humans; D066298:In Vitro Techniques; D007212:Indolizines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008099:Liver / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D013400:Sugar Acids; D054836:Indolizidines
D006026:Glycoside Hydrolases; D007212:Indolizines; D013400:Sugar Acids; C007895:gulonolactone; C037806:castanospermine; D054836:Indolizidines